Highly stereoselective hydroxy-alkylation, silylation and alkylation reactions of lithium derivatives of chiral phosphine oxides

Tetrahedron Letters

Volumn 37, Issue 41, 1996, Pages 7461-7464

  Guéguen, Catherine ^a   Mitchell, Helen J ^a   O'Brien, Peter ^a   Warren, Stuart ^a  

^a UNIVERSITY OF CAMBRIDGE   (United Kingdom)

Author keywords

[No Author keywords available]

Indexed keywords

PHOSPHINE OXIDE DERIVATIVE;

ALKYLATION; ARTICLE; DRUG SYNTHESIS; STEREOCHEMISTRY; TECHNIQUE;

EID: 0030574013     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/0040-4039(96)01611-5     Document Type: Article

References (19)

1. 1. Hall, D.; Sévin, A-F.; Warren, S. Tetrahedron Lett., 1991, 32, 7123-7126.
2. 2. Clayden, J.; Collington, E. W.; Lamont, R. B.; Warren, S. Tetrahedron Lett., 1993, 34, 2203-2206.
3. 3. Mitchell, H.; Warren, S. Tetrahedron Lett., 1996, 37, 2105-2108.
4. 4. Clayden, J.; Warren, S. Angew. Chem., Int. Ed. Engl., 1996, 35, 241-270.
5. 5. Fleming, I.; Gil, S.; Sarkar, A. K.; Schmidlin, T. J. Chem. Soc., Perkin Trans. 1, 1992, 3351-3361.
6. 6. For some examples, see: Cavalla, D.; Cruse, W. B.; Warren, S. J. Chem. Soc., Perkin Trans. 1, 1987, 1883-1898; Clayden, J.; Warren, S. J. Chem. Soc., Perkin Trans. 1, 1994, 1529-1539.
7. 6. For some examples, see: Cavalla, D.; Cruse, W. B.; Warren, S. J. Chem. Soc., Perkin Trans. 1, 1987, 1883-1898; Clayden, J.; Warren, S. J. Chem. Soc., Perkin Trans. 1, 1994, 1529-1539.
8. 7. For an alternative and stereoselective synthesis of each of the ketones anti- and syn-12, see: Cavalla, D.; Guéguen, C.; Nelson, A.; O'Brien, P.; Russell, M. G.; Warren, S. Tetrahedron Lett., 1996, 37, following paper.
9. 8. We are grateful to Dr Paul Raithby for carrying out the X-ray crystal structure analysis.
10. 1H NMR coupling constant correlation.
11. 10. Ayrey, P. M.; Warren, S. Tetrahedron Lett., 1989, 30, 4581-4584.
12. 2) 13.5 Hz.
13. 12. We have already described a synthesis of a single diastereomer of alcohol 15 starting from excess n-butyllithium, phosphine oxide 10 and ethyl benzoate (ref 10). In that paper, the major product was incorrectly assigned. Additionally, in light of the results presented in this paper, we are certain that valerophenone is an intermediate in this reaction i.e. the reaction does not proceed via ethyl benzoate acylation of 10 with subsequent addition of n-butyllithium as we had originally suggested (ref 10). To confirm this, we have repeated the reaction: phosphine oxide 10 was reacted with 5 equivalents of n-butyllithium and 2 equivalents of ethyl benzoate to give only the same alcohol syn,anti-15 (40% yield).
14. 13. Hutton, G.; Jolliff, T.; Mitchell, H.; Warren, S. Tetrahedron Lett., 1995, 36, 7905-7908.
15. 14. O'Brien, P.; Warren, S. Synlett, 1996, 579-581.
16. 15. Schwerdtfeger, J.; Hoppe, D. Angew. Chem., Int. Ed. Engl., 1992, 31, 1505-1507.
17. 16. McDougal, P. G.; Condon, B. D.; Lafosse Jr, M. D.; Lauro, A. M.; VanDerveer, D. Tetrahedron Lett., 1988, 29, 2547-2550.
18. 17. O'Brien, P.; Warren, S. Tetrahedron Lett., 1995, 36, 8473-8476; O'Brien, P.; Warren, S. Tetrahedron Lett., 1996, 37, 4271-4274.
19. 17. O'Brien, P.; Warren, S. Tetrahedron Lett., 1995, 36, 8473-8476; O'Brien, P.; Warren, S. Tetrahedron Lett., 1996, 37, 4271-4274.